Regional Sales Director, Employee Health Benefits

About Crumdale Specialty:

Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare solutions to a limited distribution network of brokers, consultants, and agents nationwide. Ranked on the Inc. 5000 Fastest Growing Companies and Best Workplaces, we leverage industry expertise, superior talent, data analytics, and a disruptive mindset to manufacture, underwrite, and administer agile, transparent, and cost-saving solutions. We optimize the fragmented health benefits supply chain to reduce health benefit costs and create better outcomes for employers and employees.

At Crumdale, people come first. We strive to make a positive impact on the people we serve. We believe this starts with the passion and purpose of our team. Our company culture is rooted in alignment, innovation, and integrity.

About the Job:

As a Regional Sales Director, you will be a cornerstone of our growth strategy. This role demands a highly driven, organized, and strategic professional with a passion for sales, broker development, and consultative solution selling. You will be responsible for building strong broker relationships, managing a robust sales pipeline, and closing high-quality business aligned with our integrated health platform.

We’re looking for a driven, broker-focused sales leader who knows how to win in the self-funded health plan space.

Requirements

• Drive regional revenue growth by developing and executing a strategic sales plan focused on health plan solutions to include level-funded, self-funded, captive, stop-loss, pharmacy solutions, and TPA solutions.
• Cultivate and expand relationships within the limited distribution network of brokers, consultants, and agents.
• Identify, develop, and close new business opportunities while strengthening existing partner relationships.
• Educate broker partners on the full suite of health plan solutions, including stop-loss, captives, and alternative funding strategies.
• Serve as a trusted advisor to brokers and consultants by delivering data-driven insights and strategic plan design recommendations.
• Collaborate cross-functionally with underwriting, actuarial, operations, and leadership teams to deliver competitive, customized proposals.
• Lead finalist presentations, strategy meetings, and executive-level discussions with brokers and employer groups.
• Maintain a disciplined pipeline management process, providing accurate forecasting and sales reporting.
• Monitor regional market trends, competitor activity, and emerging opportunities to proactively position solutions.
• Achieve and exceed assigned sales targets, growth metrics, and profitability goals.
• Ensure alignment with underwriting discipline and long-term profitability strategy.
• Represent at industry events, conferences, and broker functions to expand brand visibility and market presence.
• Uphold culture of alignment, innovation, and integrity in all external and internal interactions.

Requirements

• 5+ years of successful sales experience in self-funded health plans, stop-loss, employee benefits, or related health insurance markets.
• Demonstrated success building and managing broker/consultant relationships within a defined territory.
• Proven track record of consistently meeting or exceeding revenue and growth targets.
• Strong understanding of alternative funding arrangements, captives, cost-containment strategies, and employer health plan design.
• Ability to articulate complex health plan solutions in a clear, consultative, and value-driven manner.
• Experience navigating multi-stakeholder sales cycles and leading executive-level presentations.
• Strong pipeline management and forecasting discipline with CRM proficiency.
• Financial acumen with the ability to align growth with underwriting profitability.
• Entrepreneurial mindset with the ability to operate independently in a fast-paced, high-growth environment.
• Willingness to travel within assigned region as needed.

Success Metrics & KPIs

Performance in this role will be measured by:

• Achievement of annual new business revenue targets.
• Growth in broker/consultant partnerships within assigned territory.
• Pipeline volume, velocity, and forecast accuracy.
• Case submission activity and quote-to-bind ratio.
• Profitability and underwriting alignment of sold business.
• Retention and cross-sell/upsell penetration across full solution suite.
• Contribution to regional market share growth.
• Quality of broker engagement and brand presence in the territory.

Benefits

At Crumdale, we strive to provide a comprehensive and supportive benefits package to ensure the well-being of our employees. Our benefits include:

• Medical
• Telemedicine
• Dental
• Vision
• Life, AD&D, Disability
• 401(k)
• Flexible Time-off

Please note: Crumdale Specialty is not engaging with external recruitment agencies; please refrain from contacting us regarding this position.